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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:58 UTC
HMDB IDHMDB0015376
Secondary Accession Numbers
  • HMDB15376
Metabolite Identification
Common NameTrimeprazine
DescriptionAlimemazine, also known as trimeprazine or repeltin, belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring. Alimemazine is a drug which is used to prevent and relieve allergic conditions which cause pruritus (itching) and urticaria (some allergic skin reactions). In humans, alimemazine is involved in the alimemazine h1-antihistamine action pathway. Alimemazine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Alimemazine.
Structure
Data?1582753289
Synonyms
ValueSource
TrimeprazineKegg
RepeltinKegg
MethylpromazineKegg
AlimemazineKEGG
TrimeperazineHMDB
NedeltranMeSH, HMDB
Evans brand OF alimemazine tartrateMeSH, HMDB
PanectylMeSH, HMDB
Pierre fabre brand OF alimemazineMeSH, HMDB
Rhône poulenc rorer brand OF alimemazine tartrateMeSH, HMDB
Rhône-poulenc rorer brand OF alimemazine tartrateMeSH, HMDB
SpansuleMeSH, HMDB
ThéralèneMeSH, HMDB
IsobutrazineMeSH, HMDB
VariargilMeSH, HMDB
Alimemazine italfarmaco brandMeSH, HMDB
Allergan brand OF alimemazine tartrateMeSH, HMDB
italfarmaco Brand OF alimemazineMeSH, HMDB
VallerganMeSH, HMDB
Chemical FormulaC18H22N2S
Average Molecular Weight298.446
Monoisotopic Molecular Weight298.150369404
IUPAC Namedimethyl[2-methyl-3-(10H-phenothiazin-10-yl)propyl]amine
Traditional Nametrimeprazine
CAS Registry Number84-96-8
SMILES
CC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C12
InChI Identifier
InChI=1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3
InChI KeyZZHLYYDVIOPZBE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Para-thiazine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Thioether
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point68 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0084 g/LNot Available
LogP4.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0084 g/LALOGPS
logP4.82ALOGPS
logP4.41ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)9.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.37 m³·mol⁻¹ChemAxon
Polarizability34.83 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.60831661259
DarkChem[M-H]-171.1631661259
DeepCCS[M-2H]-193.47830932474
DeepCCS[M+Na]+169.04330932474
AllCCS[M+H]+169.532859911
AllCCS[M+H-H2O]+166.332859911
AllCCS[M+NH4]+172.532859911
AllCCS[M+Na]+173.432859911
AllCCS[M-H]-174.032859911
AllCCS[M+Na-2H]-173.532859911
AllCCS[M+HCOO]-173.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrimeprazineCC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C123348.9Standard polar33892256
TrimeprazineCC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C122307.0Standard non polar33892256
TrimeprazineCC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C122301.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Trimeprazine EI-B (Non-derivatized)splash10-0a4i-9010000000-3652afb69d877d9e3ef52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Trimeprazine EI-B (Non-derivatized)splash10-0a4i-9240000000-3d6ddecfeef1ce4ea2a22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Trimeprazine CI-B (Non-derivatized)splash10-0002-1192000000-93fd466d9dd2ccc3c6792017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Trimeprazine EI-B (Non-derivatized)splash10-0a4i-9010000000-3652afb69d877d9e3ef52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Trimeprazine EI-B (Non-derivatized)splash10-0a4i-9240000000-3d6ddecfeef1ce4ea2a22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Trimeprazine CI-B (Non-derivatized)splash10-0002-1192000000-93fd466d9dd2ccc3c6792018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimeprazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-7190000000-0f8a5eefc8992f88c42e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimeprazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimeprazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimeprazine 10V, Positive-QTOFsplash10-0f6t-0390000000-d19c7e0d929f71a4ad362016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimeprazine 20V, Positive-QTOFsplash10-0udi-3790000000-934bfb5b005b12a5e73d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimeprazine 40V, Positive-QTOFsplash10-0pc3-9310000000-63ebd221a8008ee5907e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimeprazine 10V, Negative-QTOFsplash10-0002-0190000000-2baf4399efd26ce01a1a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimeprazine 20V, Negative-QTOFsplash10-000b-0950000000-4297ad548b801681761c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimeprazine 40V, Negative-QTOFsplash10-0002-2900000000-a79d6af3311c241ede5f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimeprazine 10V, Positive-QTOFsplash10-0002-0090000000-6922163e7f4e54a0d1112021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimeprazine 20V, Positive-QTOFsplash10-0pba-7390000000-e48c69f05dd0b61fb4a32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimeprazine 40V, Positive-QTOFsplash10-0a4i-9330000000-2a742cf0712cb4007fb62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimeprazine 10V, Negative-QTOFsplash10-0002-0090000000-974be3fbdd37312b38982021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimeprazine 20V, Negative-QTOFsplash10-0002-0590000000-923a0af0890995a5d8a82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimeprazine 40V, Negative-QTOFsplash10-03ds-0970000000-966b5b52892fcd5adc272021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01246 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01246 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01246
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5373
KEGG Compound IDC07172
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlimemazine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Santos DE, Liu GJ, Takeuchi H: Blockers for excitatory effects of achatin-I, a tetrapeptide having a D-phenylalanine residue, on a snail neurone. Eur J Pharmacol. 1995 Jan 16;272(2-3):231-9. [PubMed:7713167 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]